Tetrafluorophthalic anhydride → HCID 12043697, compound

HRID 2301910Notes

Reaction equation

HRID 2301910 reaction equation
[F:1][C:2]1[C:3]([F:15])=[C:4]([F:14])[C:5]([F:13])=[C:6]2[C:11](=[O:12])[O:10][C:8](=O)[C:7]=12.[CH3:16][C@@H:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)(Cl)Cl>[CH:18]1([C@H:17]([N:24]2[C:11](=[O:12])[C:6]3[C:7](=[C:2]([F:1])[C:3]([F:15])=[C:4]([F:14])[C:5]=3[F:13])[C:8]2=[O:10])[CH3:16])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 69545Tetrafluorophthalic anhydrideHCID 6431891-Phenethylamine, (+)-

Product 1

HCID 12043697HCID 12043697, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
180 °C

Procedure

220 mg of tetrafluorophthalic anhydride and 127 mg of (R)-α-methylbenzylamine were charged in an egg-plant type flask of 50 ml, followed by stirring under heating at a temperature of 180° C. for 1.5 hours. After cooled, the reaction product was dissolved in chloroform, purified by silica gel column chromatography (eluent; methylene chloride:methanol=30:1 v/v), recrystallized from a mixed solvent of n-hexane-ethyl acetate, to obtain 210 mg of the desired product as a colorless powder. Yield: 64%. m.p. 147-148° C.; [α]20D=−5.13° (C=0.658 AcOEt); MS(EI+) 329(M)+

Workup

  1. temperatureAfter cooled
  2. custompurified by silica gel column chromatography (eluent; methylene chloride:methanol=30:1 v/v)
  3. customrecrystallized from a mixed solvent of n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-c1ec2326fbc845d3804303d03c208e5d
Source dataset
uspto-grants-2002_08
Patent number
US06429212B1

Reaction notes

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